By Desmond J. Brown, Jonathan A. Ellman, Edward C. Taylor
This publication presents the main complete, present reference at the man made chemistry of cinnolines and phthalazines. purposes to the syntheses of normal items and different chiral compounds are defined. quantity sixty four includes chapters exploring the next topics:
* fundamental Syntheses of Cinnolines
* Cinnoline, Alklycinnolines, and Arylcinnolines
* Nitro-, Amino-, and comparable Cinnolines
* Cinnolinecarboxylic Acids and comparable Derivatives
* basic Syntheses of Phthalazines
* Phthalazine, Alklyphthalazines, and Arylphthalazines
* Phthalazinecarboxylic Acids and similar Derivatives
* An Appendix of Tables of straightforward Cinnolines and straightforward Phthalazines
Read or Download Cinnolines and Phthalazines, Supplement II (The Chemistry of Heterocyclic Compounds, Volume 64) PDF
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Extra resources for Cinnolines and Phthalazines, Supplement II (The Chemistry of Heterocyclic Compounds, Volume 64)
86,123,cf. 3. FROM A PYRIDAZINE SUBSTRATE This potentially wide area of primary synthesis appears to be represented by only two types in which appropriate pyridazine substrates undergo cyclocondensation with synthones that supply either C6 þ C7 or C6 þ C7 þ C8 of the resulting cinnolines. Examples follow. 4. FROM OTHER HETEROMONOCYCLIC SUBSTRATES The formation of cinnolines from heteromonocyclic systems other than pyridazine is rare. However, at least three such systems have been so used, as illustrated in the following examples.
441 R O N NH (42) From Acylcinnolines Note: N-Acylated hydrocinnolines have been reduced to the corresponding N-alkylhydrocinnolines. 962,964 OCH2Ph OCH2Ph LiAlH4 N N CH2CH(CH2)2 OCCH2Ph (43) N N CH2CH(CH2)2 CH2CH2Ph (43a) Alkyl- and Arylcinnolines 41 From Other Alkylcinnolines Note: Modiﬁcation of existing alkyl may be done in a number of ways; some are exempliﬁed here. 636,959 CH CHNHPh N N+ I− Me (48) PhN CH3 CHNHPh (R = Me) N N+ I− R p-Me2NC6h4CHO (R = Et) (49) CH CHC6H4NMe2-p N N+ I− Et (50) By Quaternization Note: This process is often used but seldom described.
Halogeno substituents at the 3- or 4-position of cinnoline are appreciably activated by N2 and N1, respectively; those at positions 5–8 or an extranuclear position have activities only marginally better than those in corresponding carbocyclic compounds. There seems to be little difference in reactivity of a ﬂuoro, chloro, bromo, or iodo substituent at the same position. 1. 2). Other important preparative procedures are illustrated in the following examples. J. Brown Copyright # 2005 John Wiley & Sons, Inc.
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